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SYSTEMATIC NAME

IUBMB Comments

aklavinone,NADPH:oxygen oxidoreductase (12-hydroxylating)

The enzymes from the Gram-positive bacteria Streptomyces peucetius and Streptomyces purpurascens participate in the biosynthesis of daunorubicin, doxorubicin and rhodomycins. The enzyme from Streptomyces purpurascens is an FAD monooxygenase.

modifications of the aklavinone molecule can influence the efficiency of the hydroxylation carried out by DnrF. While molecules modified in positions C-10 and C-13 are hydroxylated as efficiently as aklavinone (11-deoxycarminomycinone conversion), molecules 14-hydroxylated or 4-methylated are very poor substrates (11-deoxy-4-demethyladriamycinone and 11-deoxydaunomycinone conversion)

modifications of the aklavinone molecule can influence the efficiency of the hydroxylation carried out by DnrF. While molecules modified in positions C-10 and C-13 are hydroxylated as efficiently as aklavinone (11-deoxycarminomycinone conversion), molecules 14-hydroxylated or 4-methylated are very poor substrates (11-deoxy-4-demethyladriamycinone and 11-deoxydaunomycinone conversion)

the enzyme is involved in the biosynthesis of the anthracycline antibiotic daunorubicin/doxorubicin pathway. During the biosynthesis of L-rhodomycins, RdmE first modifies aklavinone at C-11, and epsilon-rhodomycinone or aklavinone is subsequently glycosylated

the enzyme is involved in the biosynthesis of the anthracycline antibiotic daunorubicin/doxorubicin pathway. During the biosynthesis of L-rhodomycins, RdmE first modifies aklavinone at C-11, and epsilon-rhodomycinone or aklavinone is subsequently glycosylated

expression in doxorubicin-sensitive Streptomyces galilaeus ATCC 31133. Transformation of Streptomyces galilaeus ATCC 31133 with plasmid pMC213 containing the aklavinone 11-hydroxylase gene (dnrF) results in the production of many red pigments. A new metabolite is purified, and the position of the newly introduced hydroxyl group is determined. The result indicates that the aklavinone 11-hydroxylase gene is stably expressed in Streptomyces galilaeus ATCC 31133 and that it gives rise to a hybrid aclacinomycin A which shows highly specific in vitro cytotoxicity against leukemia and melanoma cell lines

heterologous expression of dnrF in Streptomyces liwidans TK23 and in Escherichia coli. Since the fusion protein does not show any hydroxylase activity, the dnrF gene is cloned into the pT7-7 vector that allows the expression of an unfused DnrF protein